"I really want to believe in Leonard, but I have these doubts he'll come through, which is a shame because I've been holding the best for last."
-Shermantine, on revealing the locations of burial sites

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Herzog and Shermantine were both born in the farming town of Linden, California, and lived a street away from each other. Because there weren't many other children to play with in their neighborhood, they befriended each other and apparently had no other friends. The two spent their childhood exploring the entire area of San Joaquin County. Shermantine's father would usually take both boys on hunting and fishing trips until they were old enough to go on their own. He would also spoil Shermantine with many gifts. Herzog had a brief affair with a woman named Kim Vanderheiden, the older sister of Cynthia Vanderheiden, who would later become one of his victims. Herzog and Shermantine remained best friends through their high school years and adulthood. They also took pleasure in bullying other people, as well as drinking and using drugs, especially methamphetamine, in their apartment in nearby Stockton. They also became frequent barflies at Cynthia and Kim's father's bar.

Shortly after graduating from Linden High School, Herzog and Shermantine committed their known killings. Howard King and Paul Cavanaugh were their first victims, both shot to death in their car. That same year, Shermantine fatally shot a man named Henry Powell. Both Powell's murder and the King-Cavanaugh case went unsolved until Herzog and Shermantine's arrests. A year later, the nude body of Robin Armtrout was found; she was raped and stabbed to death. Later, a woman named Chevelle "Chevy" Wheeler skipped class to meet with Shermantine, but she was abducted by him and presumably raped before being killed by unknown causes. During the search for Wheeler, police looked at Shermantine as a person of interest, and a search warrant for Shermantine's hunting cabin was requested. There, police found negative-type blood, and though Wheeler had negative blood, a lack of other physical evidence resulted in Shermantine not being arrested for her murder. The case went cold until DNA testings were available, which showed that the blood was most likely from Wheeler.

According to Herzog, Shermantine had also killed an unnamed Utah hunter who had crossed their way in 1994, by shooting him to death. In 1998, Cyndi Vanderheiden approached Herzog and Shermantine in a bar and asked for drugs. Instead, she was abducted by them and raped by Shermantine, then dragged to an isolated location and stabbed to death. Her body was put inside Shermantine's car and dumped in a different location. Both were arrested on March 17, 1999, for the murder of Vanderhaiden after her blood was found inside Shermantine's car. In prison, Shermantine denied any involvement with Wheeler or Vanderheiden, despite the fact that her blood was found in his car. Herzog was interrogated by police for a total of seventeen hours, during which he tried to pin all of the murders on Shermantine, gave specific details on how the victims died, informed the officers of the murder of a hunter in Utah,[1] and attempted to make himself out as an unwilling accomplice. With the accounts he provided to the investigators, he believed he would be released so he could return home, but that was not the case.

Shermantine was charged with first-degree murder regarding the deaths of King, Cavanaugh, Wheeler, and Vanderheiden. After being found guilty on all of the counts, he offered to reveal the location of Vanderheiden's body in exchange for $20,000, but this request was denied. Shermantine was sentenced to death after denying to reveal his victims' bodies in exchange for the overturning of the death penalty. Herzog was convicted for the first murders and for being present during the later murders. However, all of the charges were later thrown out when he said that his confession was coerced by police, which was corroborated by findings made by the court. Herzog's sentence was subsequently reduced to fourteen years. He was released on September 28, 2010, and moved to a trailer located near a state prison. He committed suicide in January 2012 after Leonard Padilla, a bounty hunter hired by Shermantine, informed him that his client would disclose locations of where they buried victims. Shermantine did exactly that, and Vanderheiden's body was found in Calaveras County, being identified via dental records. Along with Vanderheiden, the body of Wheeler was also found. One day later, more than 1,000 bone fragments were found in a well at an abandoned farm in Linden, some of which were matched to other victims who were previously unconnected.

Herzog and Shermantine both targeted random victims and killed only for fun and sport. They would go out "hunting", murdering random people by shooting them to death. In some instances, they abducted their female victims, raped and killed them by stabbing them with a knife, and dumped their bodies in Calaveras County.

Herzog and Shermantine were mentioned by Reid in the Season Ten episode Burn as an example of killers who experimented with different M.O.s to figure out the most satisfying way to kill a victim. Herzog was also mentioned by Hotch and Lewis in the Season Eleven episode The Job, when it was revealed that the latter interviewed him to judge his competency for trial. Lewis explained that it was initially difficult for her to get him to cooperate, but was eventually able to do so after she decided to imitate his wife's facial expressions and way of speaking.